


Don't Test Your Luck

by lydslibrary



Category: Supernatural
Genre: AU Dean Winchester - Freeform, Dean Winchester gifs, Dom!Dean Winchester, F/M, Inspired by Fifty Shades of Grey, Light Bondage, Orgasm Delay/Denial, Punishment, Rough Oral Sex, Rough Sex, Spanking, gifs, light use of riding crop, rough blowjob
Language: English
Status: Completed
Published: 2020-09-29
Updated: 2020-09-29
Packaged: 2021-03-07 16:08:55
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,437
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26710417
Author URL: https://archiveofourown.org/users/lydslibrary/pseuds/lydslibrary
Summary: Dean Winchester is a millionaire mogul CEO... and he's also your boyfriend... who does not put up with your attitude.
Relationships: Dean Winchester/You
Comments: 10
Kudos: 71





	Don't Test Your Luck

**Author's Note:**

> Made the GIFs... then got inspired. This is literally pretty much 50 Shades of Grey but with Dean Winchester... he was giving off too many Christian Grey vibes in these GIFs to not write about it. Enjoy!

“What about this one?”

Dean looked up from his phone for not even two seconds before he started shaking his head in disapproval.

“What!? What’s wrong with it?” You asked sassily, starting to get frustrated with your boyfriend’s dislike with near everything that you had tried on today. You and Dean had gone dress shopping for a charity gala that he had going on tomorrow night; it was your first major event as a public couple and you had nothing to wear. So, here you were with your millionaire mogul CEO boyfriend Dean Winchester, trying on skin-tight cocktail dresses at a high-end department store.

“Sweetheart, you bend over in that thing and the whole world can see what’s mine,” he said with a stern look on his face, warning you to watch your attitude. You rolled your eyes in frustration and Dean raised his eyebrows in return. “Roll your eyes at me again and I’ll take you over my knee right here.” It took everything you had in you to keep yourself from rolling your eyes again; you knew he’d stay true to his threat. “Try the next one on, the black one. That one looked nice,” he suggested with a soft smile before going back to his phone. You went back into the dressing room and began wiggling your way out of the suffocating dress just so you could put another one on. You and Dean had been officially dating for four months and officially fucking for about a year. You waitressed at a high-end restaurant in town and one night in came **_the_** Dean Winchester with a few colleagues. He tipped you $2,000 on a $200 meal, left you his number, and you only called to see if the tip was a mistake. The rest is history. The thing is, you and Dean didn’t have a traditional relationship. In the beginning, there was a contract involved. Now, only bits and pieces of the document remained; bound not by legal signatures but by mutual respect for one another, by communication, and by love. Love. That was something that Dean Winchester didn’t know he was capable of until he met you. You sighed as you took a look at yourself in the full-length mirror of your dressing room. You were now wearing a black skin-tight cocktail dress, although this one stopped right above your knee instead of right below your ass and didn’t show off nearly as much cleavage as the other 20 dresses that you had tried on today. You swore that at this point you were just putting on a private fashion show for Dean.

“Okay, this has to be the one,” you said, as you pulled back the dressing room curtain and stepped out, giving Dean a twirl.

“I agree, baby. Damn,” he exclaimed, as he got up from his seat on the couch and walked over to you, pulling you into his arms, “Why you’re with a guy like me, I’ll never know,” he teased, looking down at you with adoring eyes.

“I’m only here for your money,” you joked, planting a peck on his lips. Dean rolled his eyes and you gasped dramatically. “Did you just roll your eyes at me, Winchester?” You teased.

“Some things deserve an eye roll,” he chuckled.

“Yeah, whatever, you’d **_never_** take that excuse from me,” you said sassily, crossing your arms over your chest in a stance of fake offense.

“Maybe I just haven’t said anything worth an eye roll yet.”

You rolled your eyes. _Oops._ Dean raised his eyebrows in surprise. He didn’t think you’d be bold enough to do it. To be fair, it was a natural instinct of yours. Most of the time you didn’t even realize you had done it until Dean would call you out on it. In private, you had been over his knee more times than you could count for your attitude, but in public you always stopped after the first threat. You didn’t want to poke the bear on that one; there was no doubt in your mind that Dean would have pulled you over his knee in that department store, had his phone not begun to ring. Your saving grace. Dean answered his phone, shooting you a warning look that said “you just wait” before he cleared his throat and greeted whoever it was that was on the other line.

_Please be important. Please be important_ , you prayed, hoping that something came up at work and that Dean wouldn’t have the time to pull you over his knee right this second.

“Alright, I’ll be right there. Thanks,” he said roughly, before hanging up. “Something came up at work, I got to run,” he said, handing you his credit card, “Get that one and whatever else you want, I’ll call Bobby to come pick you up, okay?” He placed a tender kiss on your forehead and then leaned in so his lips were brushing up against your ear. “I wouldn’t test your luck like that again, sweetheart. You just wait until I get home.” You shuddered at his breath and at his words. He gave you a quick kiss on the lips and accompanied by an innocent smile and a “love you” before heading out of the store. You stood there for a moment trying to collect yourself; the wetness in between your legs growing as you anticipated what was waiting for you when Dean got home.

Around five, Dean texted you telling you that he’d be a few more hours. _A few more hours!?_ , you thought to yourself; he had already been gone for five. You were extremely horny; Dean’s threats from earlier did nothing but turn you on and you wanted him home now. You decided to eat something to get your mind off the way that your clit kept pulsing, begging for attention. You picked up your phone as your meal was heating up in the microwave and texted Dean back.

**Y:** **If you don’t come home soon, I’m going to take care of myself.**

**D: Was that a threat? Do it and say goodbye to cumming for a week. You’re already in trouble for the attitude you gave earlier. Don’t test me.**

You groaned and put your phone down on the kitchen counter. You didn’t want to wait, but you would. You’ve gone for a week without an orgasm, and you wouldn’t wish it upon your worst enemy.

It was around 8PM, and Dean had just texted that he’d be about 30 more minutes. You rolled your eyes, thankful that he wasn’t there to witness it. You were sitting on the couch in your pajamas; cotton shorts and a white tee with no bra on, surfing through the T.V. channels, trying to push both your sexual frustration and frustration with Dean to the back of your mind. He’d been gone for eight hours; what the fuck was he doing? Thirty minutes passed quickly and you heard the lock on the door turn. Dean stepped into the living room, a determined look on his face as he set his eyes on you.

“What the fuck took you so long?” You blurted out. You placed your hand over your mouth as soon as you said it. You didn’t mean to say it; it just came out. Your frustrations got the best of you. And now you were in _serious_ trouble, and you knew it.

“Excuse me?” Dean asked in disbelief.

“Dean, I-I’m sorry. You just – you were gone for a long time and I’ve just been sitting here trying to ignore how turned on I am and I guess I didn’t realize how frustrated it was making me and it just slipped out,” you explained. Dean didn’t say a word. His glare told you everything you needed to know before he looked away and started slowly making his way over to you.

_Fuck, fuck, fuck_ , was all you could think as you watched him walk towards you; a darkness in his eyes that had not been there moments before. In one swift motion, Dean sat down on the couch and pulled you over his knee, your pajama shorts on the ground before you could even process what was happening. His palm was rubbing gentle circles on your panty-clad ass and your breath hitched in anticipation.

“Why are you over my knee?” He growled.

“Because I cussed at you.”

“And?”

“And because I rolled my eyes,” you murmured.

“And is that polite?”

“No, sir,” you replied quietly as you bit your lip; the suspense was killing you. The first smack came down on your ass and your yelp bounced off the walls of the living room. With each additional hit you felt the heat coming off your ass and in between your legs amplify. Dean let down several hard blows with his hand and then slid your underwear down your legs. He rubbed your bare ass tenderly, slowly making his way to your soaked core. He explored your folds with his fingers, spreading your juices around them.

“It’s such a shame that you’re so wet, sweetheart, because right now I’m not in any mood to let you cum tonight.” Dean delivered a few more smacks to your ass before standing you up. “Red room. Five minutes,” he ordered as he looked up at you from his seat on the couch. He looked so damn good with his suit and smug expression; you had half the mind to get down on your knees and suck him off right there. But, an order’s an order, and you were in no position to be disobeying Dean right now. Especially if you wanted to feel a release tonight. So, you reluctantly made your way to the red room, your tingling ass on show for Dean as you walked away from him.

You took a deep breath as you entered the red room; a place where you had been able to fulfill so many of your sexual fantasies. You remembered how nervous you were when Dean brought you in here for the first time, how you flinched at every noise or touch, no matter how soft. You shed the only article of clothing that you still had on – a white tee – and tossed it into the corner of the room. You scanned the room as you began braiding your hair back, remembering the first time that you stood in this spot. “When I ask you to meet me in here, this is how you’ll be,” Dean had said as he was braiding your hair, all those months ago. It seemed like a lifetime had passed since then. You and Dean had been through more trials and tribulations than most in the year that you had been intimate together thanks to his need to do things a certain way. To love a certain way. Not that you were complaining; over time you discovered that it was the way that you needed and wanted to be loved. Not that you knew that at first, hence the trials and tribulations. You kneeled in front of the door, sitting on your heels, the red room behind you. You had this place memorized like the back of your hand. Behind you to your left was a large canopy bed. Red sheets. Behind you to your right was a dresser, full of outfits, restraints, and blindfolds, and next to it on the red wall was a display of implements. Paddles, whips, riding crops, anything you could think of, Dean had it. And used it. You placed your palms flat on your thighs and lowered your head; Dean should be in any second now.

Dean was in the kitchen sipping on a glass of water, trying to calm down before he went in to have his way with you. He wasn’t angry per say, just a little caught off guard. He wasn’t sure what to do with you; you had never snapped at him like that before. But watching you put on a little fashion show for him all day, thinking of you in all those skin-tight dresses that you had modeled for him, that alone was enough to make him want to fuck you senseless. Even if you didn’t deserve it. Dean cleared his throat and inhaled deeply, setting the glass of water on the kitchen island and making his way to the room where you were waiting for him.

The door clicked and you didn’t dare look up from your position on the floor. You could see Dean’s black shoes and dress pants walk past you. You heard rustling going on behind you, accompanied by some metal clinging. You felt just as nervous as you had the first day in this room; usually you could gauge what was in store for you. But you had never snapped at him like that before, so this time, you couldn’t. You felt Dean’s hand on your shoulder; your signal to stand. He led you over to the bed, and told you to lie down on your back, handcuffing your wrists and ankles to each bed post. You locked eyes with him as he watched you from the foot of the bed while he ripped off his tie. He looked disappointed and pissed off; never a good combo. It still made your pussy clench. Somehow, he had never been hotter.

He walked over to the side of the bed, placing the tie that he had just ripped off over your eyes and tying it behind your head. Your vision was gone, but all your other senses were heightened. You heard the soft rustling of clothes being shed, the gentle footsteps of bare feet walking across the floor, and then a small piece of soft leather traveling down the center of your body, starting right at the bottom of your neck, being slowly dragged down to your core. You bucked your hips as a shiver ran down your spine. A quick swat to your left breast with what you could tell was a riding crop reminded you to stay still.

“I was out in the kitchen thinking about how to punish you for that mouth of yours,” Dean said, landing another swat on your other breast. It took everything you had to not flinch. “But I’m just not too sure what to do. I mean, I could spank you until your ass is seven different shades of red but you’d enjoy that too much, wouldn’t you?” You whimpered as Dean delivered another swat right above your throbbing core. You could cum from his words alone if he talked to you long enough. “I asked you a question, sweetheart,” Dean growled, tapping you gently on your cheek with the crop, urging you to speak.

“Yes, sir,” you shuddered. He was right; you would enjoy it too much. You heard Dean let out a huff of air and you could picture the cocky smirk he probably had plastered across his lips.

“Yeah, I thought so,” he chuckled deeply, trailing the soft leather down to your core, brushing it over your clit before delivering a few swats to your inner thighs. You squeezed your eyes shut underneath the makeshift blindfold. You heard footsteps on the floor again and let out the breath of air that you hadn’t realized you’d been holding in. You listened intently, trying to figure out what Dean’s next move was going to be. Your muscles tensed when you heard the familiar buzzing of a vibrator and felt a dip in the bed in between your spread legs. “You move, and you won’t be cumming at all tonight. Don’t test your luck,” Dean ordered, as he placed the vibrator on your erect nipple. You nodded to show him that you understood and suppressed the urge to buck your hips again, letting out a moan instead. Dean moved the vibrator to your other nipple and you inhaled slowly; the only thing you were thinking about was not moving. It was the only thing that you could think about, because you knew the minute that you stopped thinking about it, you’d move. It was a sick psychological game that Dean was playing. If you move, you don’t get a release, but in order to stay still, you can’t pay any mind to the pleasure that he was giving you in the first place. The vibrator left you nipple and you braced yourself for what was next. You tightened every muscle in your body as you felt vibrations where you needed them the most. You knew Dean was sitting there, watching you for any movements, as he teased your clit with the toy. This was torture. You wanted to squirm, to squeeze your thighs together, to relax and enjoy this and not be so focused on staying still. You could feel your juices leaking out of you and onto the red bedsheets and you knew that if Dean kept this up, you’d be coming undone soon. You also knew that Dean wasn’t going to let you cum so fast. No, if he was going to let you cum at all tonight, he was going to draw it out. Suddenly you felt two of Dean’s fingers enter you without warning. The bastard was trying to make you move. He wanted you to break the rules again, just to give him a reason to punish you further. Not that you deserved to come tonight anyway; back when you first started fucking, cussing at Dean would have warranted at least three days without an orgasm. But that was before. Before he fell in love with you and before giving you pleasure gave him pleasure. It was almost just as much of a punishment for him to deny your orgasms as it was for you; or so he said. He claimed that he loved the noises you made when you came undone too much; that not being able to hear you make them was just as much of a punishment for him as it was for you, not having any reason to make them at all. Dean pumped his digits in and out of you while he rested the vibrator on your clit. You could feel the heat in your core rising, the familiar knot in your abdomen forming. You were close. Your pussy clenched around Dean’s fingers and he curved them slightly as he continued fucking you with them. This was unbearable. He was hitting your g-spot every time and the only reason you hadn’t cum yet was because you were so focused on not moving. Dean let out a “hmph” that told you he was rather impressed with your ability to stay still. He turned off the vibrator, a soft thump letting you know that he threw it somewhere on the bed. His fingers were still inside of you, moving in and out tantalizingly slow. You felt a dip in the bed beside your head and then Dean’s body heat draped over you like a warm blanket; he was on top of you, holding himself up by his right arm as his left hand remained at your core, continuing to play with your cunt. “You must really want to cum tonight, huh? Because you’re behaving like an angel now,” he whispered, dipping his head down until his lips were grazing over your ear.

“Yes, sir,” you breathed, trying to simultaneously remember to hold still and feel his fingers in you at the same time.

“Why is it that you decide to be a brat all day but when it comes to this room… you start listening, hm? Because the point of me punishing you for certain things is so you don’t do them again. Outside or inside of this room. I shouldn’t let you come tonight; we both know that. Do you think you deserve to cum tonight?”

“No, sir,” you murmured.

“I agree,” he said as you felt his looming body heat leave as well as the fingers that he had inside you. You whimpered. “But you might be able to earn it.” _Anything, I will literally do anything_ , you thought to yourself. You felt Dean uncuff your ankles and wrists from the bed posts, taking your hand in his as he guided you off the bed. He placed his hand on your shoulder, pushing you down to your knees. He took the tie blindfold off of you and placed his index finger and thumb under your chin, forcing you to look up at him instead of the growing bulge in his black dress pants. “You look so pretty when you’re on your knees for me, sweetheart,” he said, his voice deep and raspy as ever. You smiled at him devilishly, opening your mouth for him just enough so he could slide in his thumb. Your eyes traveled up his bare chest and locked with his as you swirled your tongue around his thumb. He smirked and pulled it out of your mouth, gently grabbing your chin with his whole hand and bending over, his face inches away from yours. You let yourself scan the beauty that it held; his chiseled jaw line, his freckles, his emerald green eyes. He was unbelievably handsome. It really wasn’t fair. “Take off my pants and suck my cock. If you do a good job, I’ll consider letting you cum tonight, how’s that sound?” You nodded enthusiastically in response and he let go of the grasp he had on your chin, allowing you to get to work. You unbuckled Dean’s belt and unbuttoned his pants, sliding them, along with his boxers, off as fast as you could. His cock sprung out from beneath them and you grabbed the base of it in your hand as you fit the rest of it in your mouth. Even with your hand covering nearly half of it, the remainder of his cock still almost hit the back of your throat with every bob of your head. After a few sucks you decided that no hands would be the way to continue; you knew Dean loved it when you used nothing but your mouth. You placed both of your hands behind your back and felt Dean grab the back of your head as he started fucking into your mouth relentlessly. Spit was running down your chin and chest, and had you not been trained out of your gag reflex with the amount of times that you’d been face fucked over the last year, you’d certainly be gagging with every thrust. “Look at me. I want you to look at me when I’m fucking that dirty little mouth of yours,” Dean grunted. You looked up at him through your eyelashes. He was biting his lip as he looked back down at you, beads of sweat forming on his forehead from how hard and fast he was slamming into your throat. It was beginning to get hard to breathe, and Dean knew this once he saw tears start to form in your eyes. “Good girl,” he praised, as he slowed down his thrusts to a moderate pace, letting you breathe a little. He pushed his cock all the way into your mouth, your nose touching his abdomen. “You think I fucked all the naughty words out of that mouth?” He asked, as he held you down on his cock. You nodded the best that you could. “For your sake, I would hope so,” he said, pulling you off of his dick by your hair. “On the bed, on your stomach. Ass up,” he ordered, and you quickly obeyed. You spread your arms out in front of you and pushed your ass up in the air, as your face and chest rested on the mattress and your legs spread apart so Dean could see everything that was his. You felt Dean get on his knees in between your legs, teasing your folds with his cock before sliding into you with ease. He thrusted into you hard, the way your body was angled allowing him to hit your g-spot every time. You wanted to reach down in between your legs and touch yourself, but you knew that wouldn’t go over well with Dean. Between all the grunts and moans and borderline screams that were being let out into the room, you heard the familiar hum of the vibrator. Dean continued to fuck into you relentlessly as he placed the vibrator on your clit, fulfilling your need to be touched. “I don’t care how good it feels, you don’t get to cum before I do,” he commanded, and you once again nodded to let him know that you understood. Not being able to cum was torturous; you must’ve forced yourself down from a climax at least three times before you felt Dean’s cock twitch inside of you, signaling that he was near his release. Holding back your orgasm was becoming unbearable, you needed to let go – and soon. A few more thrusts and you felt white streaks of cum coat your inner walls. In that moment, you finally let yourself feel everything. Dean’s cock twitching inside of you, the vibrator on your clit, the intense heat near your core – your orgasm erupted through you like a volcano. Your eyes rolled back, you screamed Dean’s name, your body shook, and your pussy clenched around Dean’s cock as you rode it out. Dean gave you a minute or two before pulling out of you, his cum dripping from your hole as he did. You collapsed onto the bed; a sweaty, heaving mess. Dean came around to the side of the bed and picked you up bridal style, as he always did after your adventures in the red room, and carried you to the bathroom. He didn’t used to do this, before. Before, he’d leave you lying on the bed to collect yourself, letting you know that there were clean clothes for you in the bathroom, whenever you were ready to clean up. Now he cleaned you up himself. He washed your hair and massaged your shoulders all while whispering sweet nothings into your ear as the warm droplets of water rained down on the both of you. You spun around to look at him, your arms wrapping around the back of his neck. He wrapped his arms around your waist in response and looked at you curiously. “What?” He asked.

“Nothing. I just love you is all.”

He beamed. “I love you too. But just a fair warning, if you _ever_ cuss at me again –”

“I don’t even want to know what’ll happen. Trust me, I won’t test my luck.”


End file.
